U.S.A. -- Will we elect an "outsider" as President? (What makes a candidate an "outsider?")

Have Americans ever elected a president who had never before held elective office?

Yes.  Three of them, in fact.

Were they elected as "outsiders?"  That is, as candidates who were outside of the existing political system, and would bring in new ideas to reform and re-energize a government that had become unresponsive to the needs of its citizens?

No.  All three already had first-hand experience with government's inner workings.  By virtue of their experience, they were a part of the existing governing system.

America is deep into its quadrennial quest for national leadership.  One--and likely only one--thing is clear: 

Memo to Senator Charles E. Schumer of New York -- Re: Iran Deal

Dear Senator Schumer,

Your Press Release dated 08.06.15 describes how you have read the recently-negotiated agreement with Iran regarding its nuclear program.  It explains your reasoning behind your decision to vote to disapprove the deal.

Respectfully, I think that your reasoning is self-defeating.

Regarding the negotiated program of inspections and validations, you find that it is better to have the deal over the next ten years than it is to not have it, and yet the opposite is true for the succeeding ten years.  So, on the merits of the agreement, it seems that you are neutral overall.

However, it is said that a bird in the hand is worth two in the bush.